| 2025 | $0.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2024 | $3,025.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2023 | $3,022.17 | Wellesley to Patriot Place (25 mile Sunday) |
| 2022 | $2,355.00 | Reimagined |
| 2021 | $3,540.00 | Reimagined |
| 2020 | $2,590.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2019 | $2,880.00 | Wellesley to Wellesley (50 mile Sunday) |
